{[(2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxooctadec-2-en-6-yl]oxy}sulfonic acid

• ChemBase ID: 165296
• Molecular Formular: C29H55N3O7S
• Molecular Mass: 589.8279
• Monoisotopic Mass: 589.37607212
• SMILES: C(CCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)CCCC(=O)C(N(C)C)C([C@@H](C/C=C/C)C)OS(=O)(=O)O
• Canonical SMILES: C/C=C/C[C@H](C(C(C(=O)CCCCCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)N(C)C)OS(=O)(=O)O)C
• InChI: InChI=1S/C29H55N3O7S/c1-10-11-16-22(6)28(39-40(36,37)38)27(32(8)9)25(34)18-15-13-12-14-17-24(33)26(21(4)5)31-29(35)23(30-7)19-20(2)3/h10-11,20-23,26-28,30H,12-19H2,1-9H3,(H,31,35)(H,36,37,38)/b11-10+/t22-,23+,26+,27?,28?/m1/s1
• InChIKey: VWWSROHUIDEJRN-MIYXVFHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxooctadec-2-en-6-yl]oxy}sulfonic acid
• IUPAC Traditional name: [(2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxooctadec-2-en-6-yl]oxysulfonic acid
• Synonyms: Cyclosporin A Hydrogen Sulfate (ester); Cyclosporine Sulfate; Cyclosporin A Sulfate

Database IDs

• CAS Number: 121673-00-5
• PubChem SID: 162259429
• PubChem CID: 71315115

CALCULATED PROPERTIES

• Acid pKa: -1.1801702
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 3.8405867
• LogD (pH = 7.4): 4.228627
• Log P: 4.2223477
• Molar Refractivity: 159.4304 cm^3
• Polarizability: 63.64129 Å^3
• Polar Surface Area: 142.11 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C988895

A metabolite of Cyclosporin A.

REFERENCES

• Masri, M., et al.: Transplant Proc., 24, 1718 (1992)